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Hilton Head Island

$129+ Cheap flights from Springfield, MA, MA to Hilton Head Island (HHH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
— HHH
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Springfield to Hilton Head Island are usually found in December or October, booked 49 days in advance, depart on a Saturday or Tuesday and return on a Monday

Cheap flight deals from Springfield to Hilton Head Island

Keep the following information in mind while searching for Springfield to Hilton Head Island flight deals. Data was last updated August 18, 2025.

Round-trip from

$249
(American Airlines)

One-way from

$129
(American Airlines)

Popular in

February

Cheapest in

December

Average price

$391
From Springfield to Hilton Head Island
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One-way flight from Springfield to Hilton Head Island
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Highest demand for flights based on searches. 12% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Springfield to Hilton Head Island

Cheapest flights from Springfield to Hilton Head Island
Explore the most affordable flight options available from Springfield to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/81:53 pmBDL - HHH
1 stop4h 24mAmerican Airlines
Tue 11/116:50 pmHHH - BDL
1 stop5h 24mAmerican Airlines
Deal found 8/17$249
This American Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:30 amBDL - HHH
1 stop5h 04mAmerican Airlines
Thu 10/26:20 pmHHH - BDL
1 stop6h 08mAmerican Airlines
Deal found 8/15$257
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:09 amBDL - HHH
1 stop5h 50mAmerican Airlines
Sun 11/166:40 pmHHH - BDL
1 stop5h 47mAmerican Airlines
Deal found 8/17$279
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:57 amBDL - HHH
1 stop6h 22mAmerican Airlines
Sun 11/236:40 pmHHH - BDL
1 stop5h 47mAmerican Airlines
Deal found 8/16$283
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:15 amBDL - HHH
1 stop5h 19mAmerican Airlines
Mon 10/63:02 pmHHH - BDL
1 stop5h 23mAmerican Airlines
Deal found 8/18$288
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:09 amBDL - HHH
1 stop4h 08mAmerican Airlines
Sun 11/96:40 pmHHH - BDL
1 stop5h 47mAmerican Airlines
Deal found 8/16$309
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/317:50 amBDL - HHH
1 stop6h 22mAmerican Airlines
Thu 9/411:04 amHHH - BDL
1 stop6h 03mAmerican Airlines
Deal found 8/16$313

Cheapflights Fare Finder

 
Customize your flight search to find flights from Springfield to Hilton Head Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
Use the filters below to find and compare flights from Springfield to Hilton Head Island that are best for you.

Fly from

Springfield

Fly to

Hilton Head Island

Route

Depart

Return

Price

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 11/8

1:53 pm-6:17 pm

1 stop4h 24m

Hilton Head Island

Tue 11/11

6:50 pm-12:14 am

1 stop5h 24m

$249

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Mon 9/29

5:30 am-10:34 am

1 stop5h 04m

Hilton Head Island

Thu 10/2

6:20 pm-12:28 am

1 stop6h 08m

$257

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 11/12

5:09 am-10:59 am

1 stop5h 50m

Hilton Head Island

Sun 11/16

6:40 pm-12:27 am

1 stop5h 47m

$279

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sun 11/16

2:02 pm-6:09 pm

1 stop4h 07m

Hilton Head Island

Sun 11/23

6:40 pm-12:27 am

1 stop5h 47m

$279

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Thu 10/2

5:15 am-10:34 am

1 stop5h 19m

Hilton Head Island

Mon 10/6

3:02 pm-8:25 pm

1 stop5h 23m

$288

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sun 11/9

6:09 am-10:17 am

1 stop4h 08m

Hilton Head Island

Sun 11/16

6:40 pm-12:27 am

1 stop5h 47m

$309

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 11/19

12:38 pm-5:50 pm

1 stop5h 12m

$129

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 10/3

5:15 am-10:34 am

1 stop5h 19m

$164

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 9/26

5:15 am-10:34 am

1 stop5h 19m

$189

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 9/12

5:15 am-10:34 am

1 stop5h 19m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Best time to book a flight from Springfield to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Springfield with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Springfield to Hilton Head Island

How far ahead should I book a flight from Springfield to Hilton Head Island?

Use this chart to determine the optimal time to book a round-trip flight from Springfield to Hilton Head Island. Price data was last updated on August 8, 2025.

Booking 49 days in advance of your planned departure date is, on average, the best time to get cheap flights from Springfield to Hilton Head Island. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilton Head Island. Reviews last updated August 18, 2025.
Read through reviews of airlines operating flights from Springfield to Hilton Head Island, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Entertainment

6.9

Comfort

7.2

Food

6.5

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Entertainment

6.9

Comfort

7.2

Food

6.5

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Springfield to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Hilton Head Island from Springfield?

    Most people fly into Hilton Head Island (HHH) if they book a flight to Hilton Head Island from Springfield. On average, Hilton Head has 0 inbound flights from Springfield per day from 5 airlines. Hilton Head Island is conveniently located just 3.3 mi from Hilton Head Island’s city center.

  • How long is the flight from Springfield to Hilton Head Island?

    A quick flight from Springfield to Hilton Head Island can take about 4h 24m. American Airlines provides one of the quickest options available for as low as $249. Springfield and Hilton Head Island are separated by a distance of 802 mi.

  • Can I find deals for flights from Springfield to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Springfield to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Springfield to Hilton Head Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Springfield to Hilton Head Island.

  • Can I find deals for business class flights from Springfield to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Springfield to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Springfield to Hilton Head Island?

    Currently, January is the cheapest month in which you can book a flight from Springfield to Hilton Head Island (average of $275). Flying from Springfield to Hilton Head Island in March is currently the most expensive (average of $480). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton

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